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Synthesis of p ‐aminobenzamides of aminopiperidazines as potential antiarrhythmic agents
Author(s) -
Kornet M. J.,
Ali K. AbdulNabi,
Steinberg Mitchell I.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310445
Subject(s) - chemistry , benzamide , purkinje fibers , procainamide , nitro compound , stereochemistry , medicinal chemistry , nitro , organic chemistry , anesthesia , electrophysiology , medicine , alkyl
1,2‐Dimethyl‐4‐aminopiperidazine ( 4 ), 1‐(2‐aminoethyl)2‐methylpiperidazine ( 11 ), 2‐(2‐aminoethyl)‐3‐meth‐yl‐2,3‐diazabicyclo[2.2.1]heptane ( 16 ), and 1,2‐dimethyl‐3‐aminomethylpiperidazine ( 21 ) have been synthesized. Amines 4, 11 , and 16 were converted to the corresponding p ‐nitrobenzamides 7,12 , and 17. Catalytic reduction of the latter nitro derivatives gave the corresponding p ‐aminobenzamides 8,13 , and 18. For comparative studies, the acyclic analog, 4‐amino‐ N [2‐(1,1,2‐trimethylhydrazino)ethyl]benzamide ( 25 ) was also synthesized. Compounds 8,13 and 25 which are analogs of procainamide were evaluated in the isolated cardiac Purkinje fiber preparation by measuring their effects on the action potential upstroke velocity.